


Night Riders

by Castiels_and_Deans_Wolf_Pack



Category: Supernatural
Genre: Alternate Universe - Western, Anal Sex, Bottom Castiel, Bottom Dean, Bottoming from the Top, Country & Western, Cowboy Castiel, Cowboy Dean, Cowboy Dean Winchester, Cowboy Sam, Drunk Sex, Enemies to Friends to Lovers, Enemies to Lovers, F/M, Farmer Castiel, Farmer Dean, Farmer Sam, First Time Bottoming, Gay Sex, Horseback Riding, Horses, Impala, M/M, Oral Sex, Outdoor Sex, Outlaw Dean, Outlaw Dean Winchester, Praise Kink, Rough Sex, Semi-Public Sex, Size Kink, Top Castiel, Top Dean, Topping from the Bottom, Voice Kink, Wall Sex
Language: English
Status: In-Progress
Published: 2017-11-01
Updated: 2018-09-10
Packaged: 2019-01-28 00:08:10
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Rape/Non-Con
Chapters: 3
Words: 2,116
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12593624
Author URL: https://archiveofourown.org/users/Castiels_and_Deans_Wolf_Pack/pseuds/Castiels_and_Deans_Wolf_Pack
Summary: Kansas 1885 - Outlaws meet at the Night Riders bar make deals.Notorious Outlaws Dean, Sam and Castiel must join forces for the train robbery of life time.Will the two famous families be able get past their dislike of each other?





	1. The Winchesters

Kansas 1885 - Travelling sucked. Dean missed the warm shelter of a house, however short lived that usually was. The country road stretched on for miles ahead though and the only town in their radius would kill them on sight. It also happened to be their hometown, once. A long time ago they lived and worked there, but now the only welcome they'd receive is a bullet to the head. 

It was Dean fault they were out here if he hadn't made that stupid deal, to get money to pay for his fathers whiskey, only it'd ended up with him caught red handed stealing gold from the local bank - a lousy set up he should've seen coming. Sammy, being Sammy had to come to his rescue and bust him out, they'd left their drunkard farther and gone on the run. 

Still, its not like they'd only bad memories of that place, the ache of homesickness may have diminished but being close to home stirred memories of their mother. She'd had to leave home too, and their were going to meet up but she'd had become a different person. The road had turned her from loving mother to, well a badass. Still Dean missed his old home.

///

It took them three days to get to the place, a surprisingly nice place considering it was in the middle of nowhere. Ellen kept the joint nice.

They rode up the gravel pathway, over to the stable. Ellen or Ash must have seen them coming, since Jo was waiting for them to help with their horses.

Chevy, Dean's mare, was a shiny black horse, her mane would flow in the wind whenever Dean rode her, and one with a lively attitude. Riot, Sam's stallion was a brown colour coat with a black tail and smooth flowing mane. The two dismounted and handed their reigns to Jo, they trusted her to look after them.

Walking slow the Winchester brothers opened the door, their hats low on their faces, as the chatter quietened down. Once inside the brothers pick a table in the far corner, hoping nobody would disturb them with deals or tasks that they didn't want any part in.

Until a short man approached the table, Dean instantly got up to head for the bar to get a drink of whiskey, for himself and for Sam.

"So, Boys. I here you're quiet good at robbing places? The names Crowley by the way. " The man - Crowley - had an odd accent that Dean or Sam couldn't figure out, but they allowed the man talk. "Hm, and what you want with us?"

"I want to give you a job, it's a very difficult job that, I think you boys would love." Crowley was now seated across from the brothers. Dean was slowly drinking from the glass that was placed in front, hat on low only half paying attention. Where as Sams had his full attention on this Crowley guy.

"So what's the place you want us to steal from?" Sam asked quietly as Crowley smiled "Ever heard of the train called Comet, the richest train. I'll give you a third of what it's worth."

"Wait, wait, wait, a third? Shouldn't we get half since its just us?" Dean spoke out from over his glass. "Ah, forgot. You're familiar to the Collins family right?"

Dean slammed his glass on the table, causing a few heads to rise up, just as Dean hissed out. "There is no way I'm taking this job if _that_ family is involved." Dean lifted himself out his chair, storming off out the door.


	2. The Collins

**Summary for the Chapter:**

> A quick backstory of Castiel Collins the outlaw.

Castiel, a young outlaw he hadn't always been an outlaw, he had been working for his families bar it wasn't until one of his older brothers, Lucifer, went off the rails to rob a bank, as the family had been in debt with the property. So the five brothers, were on the run ever since, robbing banks, trains or any other type of loot they got their hands on.

But at last all great outlaws had to come to an end. Two of his brothers, Lucifer, Michael had gotten caught only for Castiel, Gabriel and Balthazar to get outta town. Gabriel and Balthazar stuck together going off doing deals, collecting bounties to receive money. Castiel however went solo, travelling town to town doing the one thing he was good at, stealing.

Nobody knew Castiels real name, he went around known as the Dark Angel, who travelled at night to rob men on the road, with his stallion a Kiger Mustang named Dakota, the black mane would flow down the right side of the neck, as the coat was smooth and shiny Castiel adored Dakota, he had a wild lively attitude but had a kind gentle nature added to his personality.

///

Castiel spent his time at the popular bar where other criminals, and outlaws like him would go for a few drinks, girls, guys or even make dangerous deals. So that was where Castiel hung out whenever he needed to lay low and stock up on supplies, also he would spy on the two _"legendary"_ Winchester brothers.

Castiel wasn't that impressed, sure they could rob a few banks, and kill a few people but Castiel felt like he was on a whole different level then they were.

Downing his second glass of whisky, the doors of the bar opened revealing the older bowlegged Winchester, his hat was low on his face so the only part you could see were his pink pouty lips. The younger taller Winchester followed shortly after, his hat wasn't as low as the eldest Winchester had but you couldn't see his eyes.

Castiel had seen the old man Crowley snooping around the place, he was looking for more men to accept his deal, Castiel had accepted the deal but once Crowley mentioned Castiels name other men turned their noses away. When Castiels back was turned for more then ten minutes getting another glass Crowley had strutted back to the seat next to him.

"Any luck finding men to accompany me?" Castiel muttered into his glass, as Crowley hummed in response. "Two men have accepted, but your families seemed to have.. disagreed a few years back." Crowley was leaning in closer.

"So, who are these two men?" Castiel only wanted to get this job done.

"The Winchesters."


	3. Just Because We Work Together Doesn't Mean We Like You.

**Summary for the Chapter:**

> The brothers and Castiel attempt at jobs so they can hopefully work together better.

Castiel finished his third or fourth drink before strolling towards the brothers in the left side of the bar. "Well. Hello, Winchesters." Castiel brought their attention his direction.

"Collins, what a surprise!" The youngest Winchester exclaimed as the eldest sipped on his drink keeping his eyes right on Castiel. "Oh yes, what a surprise." Dean grumbled out over his glass.

"I see we're stuck working together." Castiel ignored the older as he didn't like his tone. "Yeah, seems so, by any chance did you know that guy?"

"Of course he does, we're besties." Crowley came up behind Castiel slapping him on the shoulder. Making Castiel glare over his shoulder at the man. "May you darlings do a small job for me as well? You may keep the money you get from the damn bugger." Crowley sat down besides the man still sipping his whiskey.

*----*

"So, lets see how well you can do this." Dean was trailing behind Sam the next morning while Castiel followed behind, who grunted at both boys. Dean got himself on Chevy swiftly, as well as being shocked at the type of horse Castiel had. "How the in the hell did you break one of those?" Dean watched Castiel mount the horse gracefully.

"Well, patience is needed and respect is a high need. Which is something both you boys lack with." Castiel stated kicking his horse forward to walk, being growled at by Dean and Sam while they trotted past him.

Sam was leading the road was long, Dean was at the back, with the sun right in the middle of the sky blaring down on them. "So, you know who we looking for?" Sam shouted back at Castiel.

"A guy called Smithson, he rides around doing contacts n shit hasn't paid Crowley for over a year." Castiel gave all the information he hoped the brothers would need. It was since they had shut up.

The three had to stop to give their horses a rest from the road and hot sun. Castiel slumped down on a rock pouring water on his face, Dean watched silently from patting Chevy, where as Sam was on lookout.

"So why do we have to work with you?" Dean walked over snatching Castiels water bottle from him. "Because Crowley thought it would be a good idea to get to know each other, trust me I don't like it just as much as you but I'm just trying to get a job done, ok?" Castiel took his water back from Dean who had took a sip from it.

"Get this job done then never see each other again right?" Dean glared at Castiel. "Right, now shall we go do this job or sunbathe?" Castiel smirked at Deans back when he turned stomping to his horse.

"Sammy, lets go!" Dean shouted kicking Chevy straight into trot as Castiel hurried to follow.

It took them two days to track the man down since they had to stop for the horses and sleep themselves. It was dusk when the man stopped to have a rest himself.

"How we gonna get this guy?" Dean muttered to his brother who shrugged, Castiel rolled his eyes covered half his face, he got off his horse strolling towards the man Dean and Sam were starting to protest getting off their horses, but Castiel blocked them out.

Castiel was silent on his feet walking behind Smithson turning him around as a hand came up to cover his mouth. Sam and Dean watched silently when Castiel dragged him back.

"Thought you guys knew how to do this?" Castiel snapped at the Winchesters who glared at him. "We do, we just like having a plan." Sam stepped forward attention going to the man in their possession, Dean was just constantly glaring at the floor as he was having an argument with his body.

"So you owe Crowley money, where is it?" Sam began questioning removing Castiels hand pinning the guy himself to the side of a rock. "Crowley sent you!? Shit, I don't have any money." Sam glared, asking him more questions not getting anything else from him.

"I'll do it." Castiel was swinging a blade in his hand moving towards the man as Sam stepped away. "L-listen I gave half the money away!" Castiel smirked leaning over the man.

"To who?" Castiel placed the blade lightly under the guys chin. "A man called Azazel, he been taking the money." Castiel recognised the name, but he still wasn't done. "You said half the money, where's the other half?"

"I b-bought myself a horse." The man looked down not daring to look at Castiel in the eyes. "Hmm, truth. Now." Castiel dug the blade in slightly guys the man to struggle in his hold. "Some in a bag on the horse I bought with the money, please don't kill me." The man whispered, Castiel heard footsteps that sounded like Sams walk away.

"Don't worry your not dying yet." Castiel retreated turning seeing Dean give him a nod of approval, to which Castiel nodded back walking past to get back on Dakota, his horse.

Sam walked back to his brother with a bag of money in his hands.

"That was it?" Dean scoffed glaring at the man still slumped over the rock, walking to Chevy getting his gun quietly glancing over at Castiel who was watching him with a confused glance down then smirk, making Dean glance down himself and heat up, OK so maybe watching Castiel dragging the man and questioning him made him a little hot and bothered so what!

"You may kill him, but at least take his horse maybe someone descent can ride it." Castiel turned his horse away allowing Sam and Dean to clean up.

With a bang and a thud of a body hitting the floor, Sam and Dean shuffling around before riding past with the other horse tied coming with them. "Do we need to find this Azazel guy?" Sam asked Castiel. "Lets go talk to Crowley." Castiel smirked with a snort from Dean muttering under his breath.

"What was that Dean?" Castiel snapped glaring at Dean who straightened up. "I said we may work together, but it doesn't make us buddies. OK?" Dean growled as he kicked Chevy to get her to walk a little more forward.

All men stayed silent on the ride back.

**Notes for the Chapter:**

> All these ideas come from my discord, which is also the best place to talk to me.
> 
> The discord: Supernatural Family: https://discord.gg/suyZQfC


End file.
